Organic compounds

ABSTRACT

The invention relates to the use of aminoacetonitrile compounds of formula (I), wherein R 1 , R 2 , R 3 , R 4 , R 8 , R 9 , A, m and n have the significances given in claim  1 , in the control of endoparasites, especially helminths, in warm-blooded productie livestock and domestic animals.

The present invention relates to the use of known aminoacetonitrilecompounds in the control of endoparasites, especially helminths, inwarm-blooded productive livestock and domestic animals.

Attempts have been made to control helminths, in which the endoparasiticnematodes may be the cause of serious diseases of mammals and poultry,by using a few minor classes of active ingredients, for examplemilbemycins. However, the active ingredients disclosed up until now inliterature cannot always fulfil the requirements regarding potency andactivity spectrum. There is therefore a need for active ingredients withimproved pesticidal properties. It has now been found that theaminoacetonitrile compounds described here possess outstandingproperties against endoparasites.

Aminoacetonitrile compounds with pesticidal, especially insecticidal,activity for the protection of plants are described for example in EP 0953 565 A2. It has surprisingly been shown that the following selectionof compounds of formula I also have exceptionally good activity againstendoparasites of warm-blooded animals and are tolerated extremely wellby the host animal.

The compounds correspond to the general formula

whereinR₁ signifies substituted C₁-C₄-alkylene, whereby the substituents areselected from the group comprising unsubstituted aryloxy or aryloxymono- to penta-substituted by R₅, and unsubstituted pyridyloxy orpyridyloxy mono- to tetra-substituted by R₅, whereby the substituentsmay be the same as one another or different if the number thereof isgreater than 1;R₂ signifies unsubstituted phenyl or phenyl mono- to penta-substitutedby R₅ or unsubstituted pyridyl or pyridyl mono- to tetra-substituted byR₅;R₃ and R₈ are either, independently of one another, hydrogen,C₁-C₆-alkyl or halogen-C₁-C₆alkyl; or together are C₂-C₆-alkylene;R₄ signifies hydrogen, C₁-C₆-alkyl or halogen-C₁-C₆-alkyl;R₅ signifies C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkyl,halogen-C₁-C₆-alkoxy, C₂-C₆-alkenyl, halogen-C₂-alkenyl, C₂-C₆-alkinyl,halogen-C₂-C₆-alkinyl, C₃-C₈-cycloalkyl, C₁-C₆-alkylcarbonyl,halogen-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,halogen-C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, phenyl, phenoxy, halogen,cyano or nitro;A signifies C(R₆)(R₇), CH═CH or C≡C;R₆ and R₇ either, independently of one another, signify hydrogen,halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkyl,halogen-C₁-C₆-alkoxy or C₃-C₆-cycloalkyl; or together signifyC₂-C₆-alkylene;R₉ is hydrogen or C₁-C₆-alkyl;m and n, independently of one other, are 0 or 1;and optional enantiomers thereof.

Alkyl—as a group per se and as structural element of other groups andcompounds such as halogen-alkyl, alkoxy, and alkylthio—is, in each casewith due consideration of the specific number of carbon atoms in thegroup or compound in question, either straight-chained, i.e. methyl,ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, or branched, e.g.isopropyl, isobutyl, sec.-butyl, tert.-butyl, isopentyl, neopentyl orisohexyl.

Cycloalkyl—as a group per se and as structural element of other groupsand compounds such as halocycloalkyl, cycloalkoxy andcycloalkylthio,—is, in each case with due consideration of the specificnumber of carbon atoms in the group or compound in question,cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl orcyclooctyl.

Alkenyl—as a group per se and as structural element of other groups andcompounds—is, in each case with due consideration of the specific numberof carbon atoms in the group or compound in question and of theconjugated or isolated double bonds—either straight-chained, e.g. allyl,2-butenyl, 3-pentenyl, 1-hexenyl, 1-heptenyl, 1,3-hexadienyl or1,3-octadienyl, or branched, .g. isopropenyl, isobutenyl, isoprenyl,tert.-pentenyl, isohexenyl, isoheptenyl or isooctenyl.

Alkinyl—as a group per se and as structural element of other groups andcompounds—is, in each case with due consideration of the specific numberof carbon atoms in the group or compound in question and of theconjugated or isolated double bonds—either straight-chained, e.g.propargyl, 2-butinyl, 3-pentinyl, 1-hexinyl, 1-heptinyl, 3-hexen-1-inylor 1,5-heptadien-3-inyl, or branched, e.g. 3-methylbut-1-inyl,4-ethylpent-1-inyl, 4-methylhex-2-inyl or 2-methylhept-3-inyl.

Aryloxy is phenyloxy or 1- or 2-naphthyloxy.

As a rule, halogen signifies fluorine, chlorine, bromine or iodine. Thesame applies to halogen in combination with other significances, such ashalogenalkyl or halogenphenyl.

Halogen-substituted carbon-containing groups and compounds may bepartially halogenated or perhalogenated, whereby in the case of multiplehalogenation, the halogen substituents may be identical or different.Examples of halogen-alkyl—as a group per se and as structural element ofother groups and compounds such as halogen-alkoxy orhalogen-alkylthio,—are methyl which is mono- to trisubstituted byfluorine, chlorine and/or bromine, such as CHF₂ or CF₃; ethyl which ismono- to pentasubstituted by fluorine, chlorine and/or bromine, such asCH₂CF₃, CF₂CF₃, CF₂CCl₃, CF₂CHCl₂, CF₂CHF₂, CF₂CFCl₂, CF₂CHBr₂,CF₂CHClF, CF₂CHBrF or CClFCHClF; propyl or isopropyl, mono- toheptasubstituted by fluorine, chlorine and/or bromine, such asCH₂CHBrCH₂Br, CF₂CHFCF₃, CH₂CF₂CF₃ or CH(CF₃)₂; butyl or one of itsisomers, mono- to nonasubstituted by fluorine, chlorine and/or bromine,such as CF(CF₃)CHFCF₃ or CH₂(CF₂)₂CF₃; pentyl or one of its isomerssubstituted one to eleven times by fluorine, chlorine and/or bromine,such as CF(CF₃)(CHF)₂CF₃ or CH₂(CF₂)₃CF₃; and hexyl or one of itsisomers substituted one to thirteen times by fluorine, chlorine and/orbromine, such as (CH₂)₄CHBrCH₂Br, CF₂(CHF)₄CF₃, CH₂(CF₂)₄CF₃ orC(CF₃)₂(CHF)₂CF₃.

Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms.Alkoxy is for example methoxy, ethoxy, propoxy, isopropoxy, n-butoxy,isobutoxy, sec.-butoxy and tert.-butoxy, as well as the isomerspentyloxy and hexyloxy; preferably methoxy and ethoxy. Halogenalkoxygroups preferably have a chain length of 1 to 6 carbon atoms.Halogenalkoxy is e.g. fluoromethoxy, difluoromethoxy, trifluoromethoxy,2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy,2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferablydifluoromethoxy, 2-chloroethoxy and trifluoromethoxy.

Preferred embodiments within the scope of the invention are:

(1) A compound of formula I, wherein R₁ is substituted C₁-C₄-alkylene,whereby the substituents are selected from the group comprisingunsubstituted phenyloxy or phenyloxy mono- to tri-substituted by R₅,whereby the substituents may be identical or different if the numberthereof is greater than 1; in particular substituted C₁-C₂-alkylene,whereby the substituents are selected from the group comprisingunsubstituted phenyloxy or phenyloxy mono- to tri-substituted by R₅,whereby the substituents may be identical or different if the numberthereof is greater than 1; most particularly substituted methylene,whereby the substituents are selected from the group comprisingunsubstituted phenyloxy or phenyloxy mono- to di-substituted by R₅,whereby the substituents may be identical or different if the numberthereof is greater than 1;(2) A compound of formula I, wherein R₂ is unsubstituted phenyl orphenyl mono- to penta-substituted by R₅; in particular phenyl mono- totri-substituted by R₅; most particularly phenyl mono- to di-substitutedby R₅;(3) A compound of formula I, wherein R₃ is hydrogen or C₁-C₆-alkyl;particularly hydrogen or C₁-C₄-alkyl; most particularly methyl;(4) A compound of formula I, wherein R₄ is hydrogen or C₁-C₆-alkyl;particularly hydrogen or C₁-C₂-alkyl; most particularly hydrogen;(5) A compound of formula I, wherein R₅ is C₁-C₆-alkyl, C₁-C₆-alkoxy,halogen-C₁-C₆-alkyl, halogen-C₁-C₆-alkoxy, C₂-C₆-alkenyl,halogen-C₂-C₆-alkenyl, C₂-C₆-alkinyl, halogen-C₂-C₆-alkinyl,C₃-C₈-cycloalkyl, C₁-C₆-alkylcarbonyl, halogen-C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxycarbonyl, halogen-C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylsulfonyl,C₁-C₆-alkylsulfinyl, halogen, cyano oder nitro; especially C₁-C₄-alkyl,C₁-C₄-alkoxy, halogen-C₁-C₄-alkyl, halogen-C₁-C₄-alkoxy, halogen, cyanoor nitro; most preferably C₁-C₄-alkyl, halogen-C₁-C₂-alkyl, halogen,cyano or nitro; especially halogen-C₁-C₂-alkyl or halogen;(6) A compound of formula I, in which A is C(R₆)(R₇) or CH═CH;especially C(R₆)(R₇);(7) A compound of formula I, wherein R₆ and R₇ are either, independentlyof one another, hydrogen, C₁-C₄-alkyl, or C₃-C₆-cycloalkyl; or togetherare C₂-C₆-alkylene; especially, independently of one another, hydrogenor C₁-C₂-alkyl; most particularly hydrogen;(8) A compound of formula I, wherein R₈ is hydrogen or C₁-C₆-alkyl;particularly hydrogen or C₁-C₄-alkyl; most particularly hydrogen;(9) A compound of formula I, wherein R₉ is hydrogen or C₁-C₄-alkyl;particularly hydrogen or C₁-C₂-alkyl; most particularly hydrogen;(10) A compound of formula I, wherein m is 0;(11) A compound of formula I, wherein n is 1;(12) A compound of formula I, wherein R₁ is substituted C₁-C₄-alkylene,whereby the substituents are selected from the group comprisingunsubstituted phenyloxy or phenyloxy mono- to tri-substituted by R₅,whereby the substituents may be identical or different if the numberthereof is greater than 1; R₂ is unsubstituted phenyl or phenyl mono- topenta-substituted by R₅; R₃ is hydrogen or C₁-C₆-alkyl; R₄ is hydrogenor C₁-C₆-alkyl; R₅ is C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkyl,halogen-C₁-C₄-alkoxy, halogen, cyano or nitro; A is C(R₆)(R₇) or CH═CH;R₆ and R₇ are either, independently of one another, hydrogen,C₁-C₄-alkyl, or C₃-C₆-cycloalkyl, or together are C₂-C₆-alkylene; R₈ ishydrogen or C₁-C₆-alkyl; m is 0 and n is 1;(13) A compound of formula I, wherein R₁ is substituted C₁-C₂-alkylene,whereby the substituents are selected from the group comprisingunsubstituted phenyloxy or phenyloxy mono- to tri-substituted by R₅,whereby the substituents may be identical or different if the numberthereof is greater than 1; R₂ is phenyl mono- to tri-substituted by R₅;R₃ is hydrogen or C₁-C₄-alkyl; R₄ is hydrogen or C₁-C₂-alkyl; R₅ isC₁-C₂-alkyl, halogen-C₁-C₂-alkyl, halogen, cyano or nitro; A isC(R₆)(R₇); R₆ and R₇ are, independently of one another, hydrogen orC₁-C₂-alkyl; R₈ is hydrogen or C₁-C₆-alkyl; m is 0 and n is 1; and(14) A compound of formula I, wherein R₁ is substituted methylene,whereby the substituents are selected from the group comprisingunsubstituted phenyloxy or phenyloxy mono- to di-substituted by R₅,whereby the substituents may be identical or different if the numberthereof is greater than 1; R₂ is phenyl mono- to di-substituted by R₅;R₃ is methyl, R₄ is hydrogen, R₅ is halogen-C₁-C₂-alkyl or halogen; A isC(R₆)(R₇); R₆, R₇ and R₈ are hydrogen, m is 0 and n is 1.

The compounds of formula I named in the following Table 1 are preferredin particular.

The compounds I may be present in the form of one of the possibleisomers or as a mixture thereof, e.g. depending on the number, absoluteand relative configurations of the asymmetric carbon atoms as pureisomers, such as antipodes and/or diastereoisomers, or as isomericmixtures, such as enantiomeric mixtures, e.g. racemates,diastereoisomeric mixtures or racemic mixtures; the invention relates toboth the pure isomers and all the possible isomeric mixtures, and is tobe understood as such hereinbefore and hereinafter, even ifstereochemical details are not specifically mentioned in each case.

Synthesis of the compounds is described for example in EP 0 953 565 A2.

TABLE 1

No. n R₈ R₉ phys. data 1.1 0 2-Cl 2-Cl 1.2 0 2-Cl 3-Cl 1.3 0 2-Cl 4-Clm.p. 137-9° 1.4 0 2-Cl 2,3-Cl₂ 1.5 0 2-Cl 2,4-Cl₂ 1.6 0 2-Cl 2,5-Cl₂ 1.70 2-Cl 2,6-Cl₂ m.p. 178-80° 1.8 0 2-Cl 3,4-Cl₂ 1.9 0 2-Cl 3,5-Cl₂ 1.10 02-Cl 2-CF₃ m.p. 47-49° 1.11 0 2-Cl 3-CF₃ 1.12 0 2-Cl 4-CF₃ m.p. 131-3°1.13 0 3-Cl 2-Cl 1.14 0 3-Cl 3-Cl 1.15 0 3-Cl 4-Cl 1.16 0 3-Cl 2,3-Cl₂1.17 0 3-Cl 2,4-Cl₂ 1.18 0 3-Cl 2,5-Cl₂ 1.19 0 3-Cl 2,6-Cl₂ 1.20 0 3-Cl3,4-Cl₂ 1.21 0 3-Cl 3,5-Cl₂ 1.22 0 3-Cl 2-CF₃ 1.23 0 3-Cl 3-CF₃ 1.24 03-Cl 4-CF₃ 1.25 0 4-Cl 2-Cl 1.26 0 4-Cl 3-Cl 1.27 0 4-Cl 4-Cl 1.28 04-Cl 2,3-Cl₂ 1.29 0 4-Cl 2,4-Cl₂ 1.30 0 4-Cl 2,5-Cl₂ 1.31 0 4-Cl 2,6-Cl₂1.32 0 4-Cl 3,4-Cl₂ 1.33 0 4-Cl 3,5-Cl₂ 1.34 0 4-Cl 2-CF₃ 1.35 0 4-Cl3-CF₃ 1.36 0 4-Cl 4-CF₃ 1.37 0 2,3-Cl₂ 2-Cl 1.38 0 2,3-Cl₂ 3-Cl 1.39 02,3-Cl₂ 4-Cl m.p. 190-2° 1.40 0 2,3-Cl₂ 2,3-Cl₂ 1.41 0 2,3-Cl₂ 2,4-Cl₂1.42 0 2,3-Cl₂ 2,5-Cl₂ 1.43 0 2,3-Cl₂ 2,6-Cl₂ 1.44 0 2,3-Cl₂ 3,4-Cl₂1.45 0 2,3-Cl₂ 3,5-Cl₂ 1.46 0 2,3-Cl₂ 2-CF₃ 1.47 0 2,3-Cl₂ 3-CF₃ 1.48 02,3-Cl₂ 4-CF₃ m.p. 155-7° 1.49 0 2,4-Cl₂ 2-Cl 1.50 0 2,4-Cl₂ 3-Cl m.p.122-3° 1.51 0 2,4-Cl₂ 4-Cl m.p. 143-5° 1.52 0 2,4-Cl₂ 2,3-Cl₂ 1.53 02,4-Cl₂ 2,4-Cl₂ 1.54 0 2,4-Cl₂ 2,5-Cl₂ 1.55 0 2,4-Cl₂ 2,6-Cl₂ 1.56 02,4-Cl₂ 3,4-Cl₂ 1.57 0 2,4-Cl₂ 3,5-Cl₂ 1.58 0 2,4-Cl₂ 2-CF₃ 1.59 02,4-Cl₂ 3-CF₃ 1.60 0 2,4-Cl₂ 4-CF₂ m.p. 99-102° 1.61 0 2,5-Cl₂ 2-Cl 1.620 2,5-Cl₂ 3-Cl 1.63 0 2,5-Cl₂ 4-Cl 1.64 0 2,5-Cl₂ 2,3-Cl₂ 1.65 0 2,5-Cl₂2,4-Cl₂ 1.66 0 2,5-Cl₂ 2,5-Cl₂ 1.67 0 2,5-Cl₂ 2,6-Cl₂ 1.68 0 2,5-Cl₂3,4-Cl₂ 1.69 0 2,5-Cl₂ 3,5-Cl₂ 1.70 0 2,5-Cl₂ 2-CF₃ 1.71 0 2,5-Cl₂ 3-CF₃1.72 0 2,5-Cl₂ 4-CF₃ 1.73 0 2,6-Cl₂ 2-Cl 1.74 0 2,6-Cl₂ 3-Cl 1.75 02,6-Cl₂ 4-Cl 1.76 0 2,6-Cl₂ 2,3-Cl₂ 1.77 0 2,6-Cl₂ 2,4-Cl₂ 1.78 02,6-Cl₂ 2,5-Cl₂ 1.79 0 2,6-Cl₂ 2,6-Cl₂ 1.80 0 2,6-Cl₂ 3,4-Cl₂ 1.81 02,6-Cl₂ 3,5-Cl₂ 1.82 0 2,6-Cl₂ 2-CF₃ 1.83 0 2,6-Cl₂ 3-CF₃ 1.84 0 2,6-Cl₂4-CF₃ 1.85 0 3,4-Cl₂ 2-Cl 1.86 0 3,4-Cl₂ 3-Cl 1.87 0 3,4-Cl₂ 4-Cl 1.88 03,4-Cl₂ 2,3-Cl₂ 1.89 0 3,4-Cl₂ 2,4-Cl₂ 1.90 0 3,4-Cl₂ 2,5-Cl₂ 1.91 03,4-Cl₂ 2,6-Cl₂ 1.92 0 3,4-Cl₂ 3,4-Cl₂ 1.93 0 3,4-Cl₂ 3,5-Cl₂ 1.94 03,4-Cl₂ 2-CF₃ 1.95 0 3,4-Cl₂ 3-CF₃ 1.96 0 3,4-Cl₂ 4-CF₃ m.p. 93-5° 1.970 3,5-Cl₂ 2-Cl 1.98 0 3,5-Cl₂ 3-Cl 1.99 0 3,5-Cl₂ 4-Cl 1.100 0 3,5-Cl₂2,3-Cl₂ 1.101 0 3,5-Cl₂ 2,4-Cl₂ 1.102 0 3,5-Cl₂ 2,5-Cl₂ 1.103 0 3,5-Cl₂2,6-Cl₂ 1.104 0 3,5-Cl₂ 3,4-Cl₂ 1.105 0 3,5-Cl₂ 3,5-Cl₂ 1.106 0 3,5-Cl₂2-CF₃ 1.107 0 3,5-Cl₂ 3-CF₃ 1.108 0 3,5-Cl₂ 4-CF₃ 1.109 0 2-CF₃ 2-Cl1.110 0 2-CF₃ 3-Cl 1.111 0 2-CF₃ 4-Cl 1.112 0 2-CF₃ 2,3-Cl₂ 1.113 02-CF₃ 2,4-Cl₂ 1.114 0 2-CF₃ 2,5-Cl₂ 1.115 0 2-CF₃ 2,6-Cl₂ m.p. 168-70°1.116 0 2-CF₃ 3,4-Cl₂ 1.117 0 2-CF₃ 3,5-Cl₂ 1.118 0 2-CF₃ 2-CF₃ 1.119 02-CF₃ 3-CF₃ 1.120 0 2-CF₃ 4-CF₃ m.p. 148.5° 1.121 0 3-CF₃ 2-Cl 1.122 03-CF₃ 3-Cl 1.123 0 3-CF₃ 4-Cl 1.124 0 3-CF₃ 2,3-Cl₂ 1.125 0 3-CF₃2,4-Cl₂ 1.126 0 3-CF₃ 2,5-Cl₂ 1.127 0 3-CF₃ 2,6-Cl₂ 1.128 0 3-CF₃3,4-Cl₂ 1.129 0 3-CF₃ 3,5-Cl₂ 1.130 0 3-CF₃ 2-CF₃ 1.131 0 3-CF₃ 3-CF₃1.132 0 3-CF₃ 4-CF₃ 1.133 0 4-CF₃ 2-Cl 1.134 0 4-CF₃ 3-Cl m.p. 160-2°1.135 0 4-CF₃ 4-Cl m.p. 147-9° 1.136 0 4-CF₃ 2,3-Cl₂ 1.137 0 4-CF₃2,4-Cl₂ 1.138 0 4-CF₃ 2,5-Cl₂ 1.139 0 4-CF₃ 2,6-Cl₂ 1.140 0 4-CF₃3,4-Cl₂ 1.141 0 4-CF₃ 3,5-Cl₂ 1.142 0 4-CF₃ 2-CF₃ 1.143 0 4-CF₃ 3-CF₃1.144 0 4-CF₃ 4-CF₃ m.p. 140-3° 1.145 1 2-Cl 2-Cl 1.146 1 2-Cl 3-Cl1.147 1 2-Cl 4-Cl 1.148 1 2-Cl 2,3-Cl₂ 1.149 1 2-Cl 2,4-Cl₂ 1.150 1 2-Cl2,5-Cl₂ 1.151 1 2-Cl 2,6-Cl₂ 1.152 1 2-Cl 3,4-Cl₂ 1.153 1 2-Cl 3,5-Cl₂1.154 1 2-Cl 2-CF₃ 1.155 1 2-Cl 3-CF₃ 1.156 1 2-Cl 4-CF₃ 1.157 1 3-Cl2-Cl 1.158 1 3-Cl 3-Cl 1.159 1 3-Cl 4-Cl 1.160 1 3-Cl 2,3-Cl₂ 1.161 13-Cl 2,4-Cl₂ 1.162 1 3-Cl 2,5-Cl₂ 1.163 1 3-Cl 2,6-Cl₂ 1.164 1 3-Cl3,4-Cl₂ 1.165 1 3-Cl 3,5-Cl₂ 1.166 1 3-Cl 2-CF₃ 1.167 1 3-Cl 3-CF₃ 1.1681 3-Cl 4-CF₃ 1.169 1 4-Cl 2-Cl 1.170 1 4-Cl 3-Cl 1.171 1 4-Cl 4-Cl 1.1721 4-Cl 2,3-Cl₂ 1.173 1 4-Cl 2,4-Cl₂ 1.174 1 4-Cl 2,5-Cl₂ 1.175 1 4-Cl2,6-Cl₂ 1.176 1 4-Cl 3,4-Cl₂ 1.177 1 4-Cl 3,5-Cl₂ 1.178 1 4-Cl 2-CF₃1.179 1 4-Cl 3-CF₃ 1.180 1 4-Cl 4-CF₃ 1.181 1 2,3-Cl₂ 2-Cl 1.182 12,3-Cl₂ 3-Cl 1.183 1 2,3-Cl₂ 4-Cl 1.184 1 2,3-Cl₂ 2,3-Cl₂ 1.185 12,3-Cl₂ 2,4-Cl₂ 1.186 1 2,3-Cl₂ 2,5-Cl₂ 1.187 1 2,3-Cl₂ 2,6-Cl₂ 1.188 12,3-Cl₂ 3,4-Cl₂ 1.189 1 2,3-Cl₂ 3,5-Cl₂ 1.190 1 2,3-Cl₂ 2-CF₃ 1.191 12,3-Cl₂ 3-CF₃ 1.192 1 2,3-Cl₂ 4-CF₃ 1.193 1 2,4-Cl₂ 2-Cl 1.194 1 2,4-Cl₂3-Cl m.p. 151-3° 1.195 1 2,4-Cl₂ 4-Cl m.p. 102-4° 1.196 1 2,4-Cl₂2,3-Cl₂ 1.197 1 2,4-Cl₂ 2,4-Cl₂ 1.198 1 2,4-Cl₂ 2,5-Cl₂ 1.199 1 2,4-Cl₂2,6-Cl₂ 1.200 1 2,4-Cl₂ 3,4-Cl₂ 1.201 1 2,4-Cl₂ 3,5-Cl₂ 1.202 1 2,4-Cl₂2-CF₃ 1.203 1 2,4-Cl₂ 3-CF₃ 1.204 1 2,4-Cl₂ 4-CF₃ m.p. 94-6° 1.205 12,5-Cl₂ 2-Cl 1.206 1 2,5-Cl₂ 3-Cl 1.207 1 2,5-Cl₂ 4-Cl 1.208 1 2,5-Cl₂2,3-Cl₂ 1.209 1 2,5-Cl₂ 2,4-Cl₂ 1.210 1 2,5-Cl₂ 2,5-Cl₂ 1.211 1 2,5-Cl₂2,6-Cl₂ 1.212 1 2,5-Cl₂ 3,4-Cl₂ 1.213 1 2,5-Cl₂ 3,5-Cl₂ 1.214 1 2,5-Cl₂2-CF₃ 1.215 1 2,5-Cl₂ 3-CF₃ 1.216 1 2,5-Cl₂ 4-CF₃ 1.217 1 2,6-Cl₂ 2-Cl1.218 1 2,6-Cl₂ 3-Cl 1.219 1 2,6-Cl₂ 4-Cl 1.220 1 2,6-Cl₂ 2,3-Cl₂ 1.2211 2,6-Cl₂ 2,4-Cl₂ 1.222 1 2,6-Cl₂ 2,5-Cl₂ 1.223 1 2,6-Cl₂ 2,6-Cl₂ 1.2241 2,6-Cl₂ 3,4-Cl₂ 1.225 1 2,6-Cl₂ 3,5-Cl₂ 1.226 1 2,6-Cl₂ 2-OF₃ 1.227 12,6-Cl₂ 3-CF₃ 1.228 1 2,6-Cl₂ 4-OF₃ 1.229 1 3,4-Cl₂ 2-Cl 1.230 1 3,4-Cl₂3-Cl 1.231 1 3,4-Cl₂ 4-Cl 1.232 1 3,4-Cl₂ 2,3-Cl₂ 1.233 1 3,4-Cl₂2,4-Cl₂ 1.234 1 3,4-Cl₂ 2,5-Cl₂ 1.235 1 3,4-Cl₂ 2,6-Cl₂ 1.236 1 3,4-Cl₂3,4-Cl₂ 1.237 1 3,4-Cl₂ 3,5-Cl₂ 1.238 1 3,4-Cl₂ 2-CF₃ 1.239 1 3,4-Cl₂3-0 F3 1.240 1 3,4-Cl₂ 4-OF₃ 1.241 1 3,5-Cl₂ 2-Cl 1.242 1 3,5-Cl₂ 3-Cl1.243 1 3,5-Cl₂ 4-Cl 1.244 1 3,5-Cl₂ 2,3-Cl₂ 1.245 1 3,5-Cl₂ 2,4-Cl₂1.246 1 3,5-Cl₂ 2,5-Cl₂ 1.247 1 3,5-Cl₂ 2,6-Cl₂ 1.248 1 3,5-Cl₂ 3,4-Cl₂1.249 1 3,5-Cl₂ 3,5-Cl₂ 1.250 1 3,5-Cl₂ 2-CF₃ 1.251 1 3,5-Cl₂ 3-CF₃1.252 1 3,5-Cl₂ 4-CF₃ 1.253 1 2-CF₃ 2-Cl 1.254 1 2-CF₃ 3-Cl 1.255 12-CF₃ 4-Cl 1.256 1 2-CF₃ 2,3-Cl₂ 1.257 1 2-OF₃ 2,4-Cl₂ 1.258 1 2-CF₃2,5-Cl₂ 1.259 1 2-CF₃ 2,6-Cl₂ 1.260 1 2-CF₃ 3,4-Cl₂ 1.261 1 2-CF₃3,5-Cl₂ 1.262 1 2-CF₃ 2-CF₃ 1.263 1 2-CF₃ 3-CF₃ 1.264 1 2-CF₃ 4-CF₃1.265 1 3-CF₃ 2-Cl 1.266 1 3-CF₃ 3-Cl 1.267 1 3-CF₃ 4-Cl 1.268 1 3-CF₃2,3-Cl₂ 1.269 1 3-CF₃ 2,4-Cl₂ 1.270 1 3-CF₃ 2,5-Cl₂ 1.271 1 3-CF₃2,6-Cl₂ 1.272 1 3-CF₃ 3,4-Cl₂ 1.273 1 3-CF₃ 3,5-Cl₂ 1.274 1 3-CF₃ 2-CF₃1.275 1 3-CF₃ 3-CF₃ 1.276 1 3-CF₃ 4-CF₃ 1.277 1 4-CF₃ 2-Cl 1.278 1 4-CF₃3-Cl m.p. 136-8° 1.279 1 4-CF₃ 4-Cl m.p. 133-5° 1.280 1 4-CF₃ 2,3-Cl₂1.281 1 4-CF₃ 2,4-Cl₂ 1.282 1 4-CF₃ 2,5-Cl₂ 1.283 1 4-CF₃ 2,6-Cl₂ 1.2841 4-CF₃ 3,4-Cl₂ 1.285 1 4-CF₃ 3,5-Cl₂ 1.286 1 4-CF₃ 2-CF₃ 1.287 1 4-CF₃3-CF₃ 1.288 1 4-CF₃ 4-CF₃ m.p. 126-8°

TABLE 2

No. A R₈ R₂ phys. data 2.1 — H C₆H₄-4-CF₃ m.p. 137° 2.2 — 2-F C₆H₄-4-CF₃m.p. 155° 2.3 — 2-Cl C₆H₄-2-F 2.4 — 2-Cl C₆H₄-4-F 2.5 — 2-Cl C₆H₄-4-CH₃2.6 — 2-Cl C₆H₄-4-C(O)CH₃ m.p. 135-7° 2.7 — 2-Cl C₆H₃-2,6-F₂ m.p.108-11° 2.8 — 2-Cl C₆H₃-2-F-4-CF₃ 2.9 — 2-CF₃ C₆H₃-2,6-F₂ m.p. 40-4°2.10 — 2-CF₃ C₆H₄-4-CH₃ m.p. 147-50° 2.11 — 2-CF₃ C₆H₄-4-t-C₄H₉ m.p.160-3° 2.12 — 2-CF₃ C₆H₄-4-OCH₃ m.p. 180-2° 2.13 — 2-CF₃ C₆H₄-4-OC₆H₅m.p. 45-9° 2.14 — 2-CF₃ C₆H₄-4-SCF₃ m.p. 78-82° 2.15 — 2-CF₃ C₆H₄-4-m.p. 144-6° C(O)OCH₃ 2.16 — 2-CF₃ C₆H₄-4-C(O)CF₃ m.p. 52-6° 2.17 — 2-CF₃C₆H₄-4-C₆H₅ m.p. 137-40° 2.18 — 2-CF₃ C₆H₃-2,4-(CF₃)₂ m.p. 49-52° 2.19 —2-CF₃ C₆H₃-2-F-4-CF₃ 2.20 — 2-CF₃ C₆H₃-3-F-4-CF₃ m.p. 149-50° 2.21 —2-CF₃ 3-C₅H₃N-6-Cl m.p. 138-40° 2.22 — 2-OCH₃ C₆H₄-4-CF₃ m.p. 86° 2.23 —2-OCF₃ C₆H₄-4-CF₃ m.p. 105° 2.24 — 4-S(O₂)CH₃ C₆H₄-4-CF₃ 2.25 —2-C(O)OCH₃ C₆H₄-4-CF₃ m.p. 118° 2.26 — 2,4-F₂ C₆H₄-4-CF₃ m.p. 130° 2.27— 2,5-F₂ C₆H₄-4-CF₃ m.p. 125° 2.28 — 2,5-Cl₂ C₆H₄-4-CF₃ m.p. 140° 2.29 —2-Cl, 4-CH₃ C₆H₄-4-CF₃ m.p. 133° 2.30 — 2-Cl, 5-CH₃ C₆H₄-4-C(O)CF₃ m.p.46-50° 2.31 — 2-Cl, 5-CH₃ C₆H₄-4-CF₃ m.p. 141° 2.32 — 2-Cl, 4-CF₃C₆H₄-4-CF₃ m.p. 146° 2.33 — 2-Cl, 4-OCH₃ C₆H₄-4-CF_(3.) m.p. 122° 2.34 —2,5-(CH₃)₂ C₆H₄-4-CF₃ m.p. 71° 2.35 — 2-F, 5-CH₃ C₆H₄-4-CF₃ m.p. 133°2.36 — 2-F, 5-CF₃ C₆H₄-4-CF₃ m.p. 127° 2.37 — 2,3,6-F₃ C₆H₄-4-CF₃ m.p.150-1° 2.38 CH₂CH₂ 2-Cl C₆H₅ m.p. 120-2° 2.39 CH₂CH₂ 2-CF₃ C₆H₃-2,3-Cl₂m.p. 128-30° 2.40 CH═CH 2-Cl C₆H₄-4-CF₃ 2.41 CH═CH 2-CF₃ C₆H₄-2-CF₃ m.p.102-4° 2.42 1,1- 2-Cl C₆H₄-4-Cl m.p. 104-7° cyclobutyl 2.43 CH₂CH₂CH₂2-CF₃ C₆H₅ m.p. 99-103°

The compounds I according to the invention are notable for their broadactivity spectrum and are valuable active ingredients in the field ofpest control, including in particular the control of endoparasites,particularly helminths, on animals, whilst being well-tolerated bywarm-blooded animals, fish and plants. These include the endoparasiticnematodes which may be the cause of serious diseases of mammals andpoultry, e.g. sheep, pigs, goats, cattle, horses, donkeys, dogs, cats,guinea-pigs and exotic birds. Typical nematodes of this indication are:Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia,Ascaris, Bunostonum, Oesophagostonum, Charbertia, Trichuris, Strongylus,Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia,Oxyuris, Ancylostoma, Uncinaria, Toxascaris and Parascaris. Theparticular advantage of the compounds of formula I is their efficacyagainst those parasites that are resistant towards active ingredientsbased on benzimidazole.

Certain pests of the species Nematodirus, Cooperia and Oesophagostonuminfest the intestinal tract of the host animal, while others of thespecies Haemonchus and Ostertagia are parasitic in the stomach and thoseof the species Dictyocaulus are parasitic in the lung tissue. Parasitesof the families Filariidae and Setariidae may be found in the internalcell tissue and in the organs, e.g. the heart, the blood vessels, thelymph vessels and the subcutaneous tissue. A particularly notableparasite is the heartworm of the dog, Dirofilaria immitis. The compoundsof formula I are highly effective against these parasites.

Furthermore, the compounds of formula I are suitable for the control ofhuman pathogenic parasites. Of these, typical representatives thatappear in the digestive tract are those of the species Ancylostoma,Necator, Ascaris, Strongyloides, Trichinella, Capillaria, Trichuris andEnterobius. The compounds of the present invention are also effectiveagainst parasites of the species Wuchereria, Brugia, Onchocerca and Loafrom the family of Filariidae, which appear in the blood, in the tissueand in various organs, and also against Dracunculus and parasites of thespecies Strongyloides and Trichinella, which infect the gastrointestinaltract in particular.

The good pesticidal activity of the compounds of formula I correspondsto a mortality rate of at least 50-60% of the pests mentioned. Inparticular, the compounds of formula I are notable for the exceptionallylong duration of efficacy.

The compounds of formula I are preferably employed in unmodified form orpreferably together with the adjuvants conventionally used in the art offormulation and may therefore be processed in a known manner to give,for example, emulsifiable concentrates, directly dilutable solutions,dilute emulsions, soluble powders, granules or microencapsulations inpolymeric substances. As with the compositions, the methods ofapplication are selected in accordance with the intended objectives andthe prevailing circumstances.

The formulation, i.e. the agents, preparations or compositionscontaining the active ingredient of formula I, or combinations of theseactive ingredients with other active ingredients, and optionally a solidor liquid adjuvant, are produced in a manner known per se, for exampleby intimately mixing and/or grinding the active ingredients withspreading compositions, for example with solvents, solid carriers, andoptionally surface-active compounds (surfactants).

The solvents in question may be: alcohols, such as ethanol, propanol orbutanol, and glycols and their ethers and esters, such as propyleneglycol, dipropylene glycol ether, ethylene glycol, ethylene glycolmonomethyl or -ethyl ether, ketones, such as cyclohexanone, isophoroneor diacetanol alcohol, strong polar solvents, such asN-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, orwater, vegetable oils, such as rape, castor, coconut, or soybean oil,and also, if appropriate, silicone oils.

Preferred application forms for usage on warm-blooded animals in thecontrol of helminths include solutions, emulsions, suspensions(drenches), food additives, powders, tablets including effervescenttablets, boll, capsules, micro-capsules and pour-on formulations,whereby the physiological comparability of the formulation excipientsmust be taken into consideration.

The binders for tablets and boll may be chemically modified polymericnatural substances that are soluble in water or in alcohol, such asstarch, cellulose or protein derivatives (e.g. methyl cellulose,carboxymethyl cellulose, ethylhydroxyethyl cellulose, proteins such aszein, gelatin and the like), as well as synthetic polymers, such aspolyvinyl alcohol, polyvinyl pyrrolidone etc. The tablets also containfillers (e.g. starch, microcrystalline cellulose, sugar, lactose etc.),glidants and disintegrants.

If the anthelminthics are present in the form of feed concentrates, thenthe carriers used are e.g. performance feeds, feed grain or proteinconcentrates. Such feed concentrates or compositions may contain, apartfrom the active ingredients, also additives, vitamins, antibiotics,chemotherapeutics or other pesticides, primarily bacteriostats,fungistats, coccidiostats, or even hormone preparations, substanceshaving anabolic action or substances which promote growth, which affectthe quality of meat of animals for slaughter or which are beneficial tothe organism in another way. If the compositions or the activeingredients of formula I contained therein are added directly to feed orto the drinking troughs, then the formulated feed or drink contains theactive ingredients preferably in a concentration of ca. 0.0005 to 0.02%by weight (5-200 ppm).

The compounds of formula I according to the invention may be used aloneor in combination with other biocides. They may be combined withpesticides having the same sphere of activity e.g. to increase activity,or with substances having another sphere of activity e.g. to broaden therange of activity. It can also be sensible to add so-called repellents.If the range of activity is to be extended to endoparasites, e.g.wormers, the compounds of formula I are suitably combined withsubstances having endoparasitic properties. Of course, they can also beused in combination with antibacterial compositions. Since the compoundsof formula I are adulticides, i.e. since they are effective inparticular against the adult stage of the target parasites, the additionof pesticides which instead attack the juvenile stages of the parasitesmay be very advantageous. In this way, the greatest part of thoseparasites that produce great economic damage will be covered. Moreover,this action will contribute substantially to avoiding the formation ofresistance. Many combinations may also lead to synergistic effects, i.e.the total amount of active ingredient can be reduced, which is desirablefrom an ecological point of view. Preferred groups of combinationpartners and especially preferred combination partners are named in thefollowing, whereby combinations may contain one or more of thesepartners in addition to a compound of formula I.

Suitable partners in the mixture may be biocides, e.g. the insecticidesand acaricides with a varying mechanism of activity, which are named inthe following and have been known to the person skilled in the art for along time, e.g. chitin synthesis inhibitors, growth regulators; activeingredients which act as juvenile hormones; active ingredients which actas adulticides; broad-band insecticides, broad-band acaricides andnematicides; and also the well known anthelminthics and insect- and/oracarid-deterring substances, said repellents or detachers.

Non-limitative examples of suitable insecticides and acaricides are:

1. Abamectin 2. AC 303 630 3. Acephat 4. Acrinathrin 5. Alanycarb 6.Aldicarb 7. α-Cypermethrin 8. Alphamethrin 9. Amitraz 10. Avermectin B₁11. AZ 60541 12. Azinphos A 13. Azinphos M 14. Azinphos-methyl 15.Azocyclotin 16. Bacillus subtil. toxin 17. Bendiocarb 18. Benfuracarb19. Bensultap 20. β-Cyfluthrin 21. Bifenthrin 22. BPMC 23. Brofenprox24. Bromophos A 25. Bufencarb 26. Buprofezin 27. Butocarboxin 28.Butylpyridaben 29. Cadusafos 30. Carbaryl 31. Carbofuran 32.Carbophenthion 33. Cartap 34. Chloethocarb 35. Chlorethoxyfos 36.Chlorfenapyr 37. Chlorfluazuron 38. Chlormephos 39. Chlorpyrifos 40.Cis-Resmethrin 41. Clocythrin 42. Clofentezin 43. Cyanophos 44.Cycloprothrin 45. Cyfluthrin 46. Cyhexatin 47. D 2341 48. Deltamethrin49. Demeton M 50. Demeton S 51. Demeton-S-methyl 52. Dibutylaminothio53. Dichlofenthion 54. Dicliphos 55. Diethion 56. Diflubenzuron 57.Dimethoat 58. Dimethylvinphos 59. Dioxathion 60. DPX-MP062 61.Edifenphos 62. Emamectin 63. Endosulfan 64. Esfenvalerat 65.Ethiofencarb 66. Ethion 67. Ethofenprox 68. Ethoprophos 69. Etrimphos70. Fenamiphos 71. Fenazaquin 72. Fenbutatinoxid 73. Fenitrothion 74.Fenobucarb 75. Fenothiocarb 76. Fenoxycarb 77. Fenpropathrin 78.Fenpyrad 79. Fenpyroximate 80. Fenthion 81. Fenvalerate 82. Fipronil 83.Fluazinam 84. Fluazuron 85. Flucycloxuron 86. Flucythrinat 87.Flufenoxuron 88. Flufenprox 89. Fonophos 90. Formothion 91. Fosthiazat92. Fubfenprox 93. HCH 94. Heptenophos 95. Hexaflumuron 96. Hexythiazox97. Hydroprene 98. Imidacloprid 99. Insekten-aktive Pilze 100.Insekten-aktive Nematoden 101. Insekten-aktive Viren 102. Iprobenfos103. Isofenphos 104. Isoprocarb 105. Isoxathion 106. Ivermectin 107.λ-Cyhalothrin 108. Lufenuron 109. Malathion 110. Mecarbam 111.Mesulfenphos 112. Metaldehyd 113. Methamldophos 114. Methiocarb 115.Methomyl 116. Methoprene 117. Metolcarb 118. Mevinphos 119. Milbemectin120. Moxidectin 121. Naled 122. NC 184 123. NI-25, Acetamiprid 124.Nitenpyram 125. Omethoat 126. Oxamyl 127. Oxydemethon M 128. Oxydeprofos129. Parathion 130. Parathion-methyl 131. Permethrin 132. Phenthoat 133.Phorat 134. Phosalone 135. Phosmet 136. Phoxim 137. Pirimicarb 138.Pirimiphos A 139. Pirimiphos M 140. Promecarb 141. Propaphos 142.Propoxur 143. Prothiofos 144. Prothoat 145. Pyrachlophos 146.Pyradaphenthion 147. Pyresmethrin 148. Pyrethrum 149. Pyridaben 150.Pyrimidifen 151. Pyriproxyfen 152. RH 5992 153. RH-2485 154. Salithion155. Sebufos 156. Silafluofen 157. Spinosad 158. Sulfotep 159. Sulprofos160. Tebufenozide 161. Tebufenpyrad 162. Tebupirimphos 163.Teflubenzuron 164. Tefluthrin 165. Temephos 166. Terbam 167. Terbufos168. Tetrachlorvinphos 169. Thiafenox 170. Thiodicarb 171. Thiofanox172. Thionazin 173. Thuringiensin 174. Tralomethrin 175. Triarthen 176.Triazamate 177. Triazophos 178. Triazuron 179. Trichlorfon 180.Triflumuron 181. Trimethacarb 182. Vamidothion 183. XMC(3,5,-Xy-lylmethylcarbamat) 184. Xylylcarb 185. YI 5301/5302 186.ζ-Cypermethrin 187. Zetamethrin

Non-limitative examples of suitable anthelminthics are named in thefollowing, a few representatives have insecticidal and acaricidalactivity in addition to the anthelminthic activity, and are partlyalready in the above list.

-   (A1)    Praziquantel=2-cyclohexylcarbonyl-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-α]isoquinoline-   (A2)    Closantel=3,5-diiodo-N-[5-chloro-2-methyl-4-(a-cyano-4-chlorobenzyl)phenyl]-salicylamide-   (A3)    Triclabendazole=5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole-   (A4)    Levamisol=L-(−)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1b]thiazole-   (A5) Mebendazole=(5-benzoyl-1H-benzimidazol-2-yl)carbaminic acid    methylester-   (A6) Omphalotin=a macrocyclic fermentation product of the fungus    Omphalotus oleanus described in WO 97/20857-   (A7) Abamectin=avermectin B1-   (A8) Ivermectin=22,23-dihydroavermectin B1-   (A9) Moxidectin    5-O-demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)-milbemycin    B-   (A10)    Doramectin=25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)-avermectin    A1a-   (A11) Milbemectin=mixture of milbemycin A3 and milbemycin A4-   (A12) Milbemycinoxim=5-oxime of milbemectin

Non-limitative examples of suitable repellents and detachers are:

-   (R1) DEET (N,N-diethyl-m-toluamide)-   (R2) KBR 3023 N-butyl-2-oxycarbonyl-(2-hydroxy)-piperidine-   (R3)    Cymiazole=N,-2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene-2,4-xylidene

The said partners in the mixture are best known to specialists in thisfield. Most are described in various editions of the Pesticide Manual,The British Crop Protection Council, London, and others in the variouseditions of The Merck Index, Merck & Co., Inc., Rahway, N.J., USA or inpatent literature. Therefore, the following listing is restricted to afew places where they may be found by way of example.

-   (I) 2-Methyl-2-(methylthio)propionaldehyde-O-methylcarbamoyloxime    (Aldicarb), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 26;-   (II)    S-(3,4-dihydro-4-oxobenzo[d]-[1,2,3]-triazin-3-ylmethyl)O,O-dimethyl-phosphoro-dithioate    (Azinphos-methyl), from The Pesticide Manual, 11^(th) Ed. (1997),    The British Crop Protection Council, London, page 67;-   (III)    Ethyl-N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl-(methyl)aminothio]-N-isopropyl-β-alaninate    (Benfuracarb), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 96;-   (IV)    2-Methylbiphenyl-3-ylmethyl-(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate    (Bifenthrin), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 118;-   (V) 2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazian-4-one    (Buprofezin), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 157;-   (VI) 2,3-Dihydro-2,2-dimethylbenzofuran-7-yl-methylcarbamate    (Carbofuran), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 186;-   (VII)    2,3-Dihydro-2,2-dimethylbenzofuran-7-yl-(dibutylaminothio)methylcarbamate    (Carbosulfan), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 188;-   (VIII) S,S′-(2-dimethylaminotrimethylene)-bis(thiocarbamate)    (Cartap), from The Pesticide Manual, 11^(th) Ed. (1997), The British    Crop Protection Council, London, page 193;-   (IX)    1-[3,5-Dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluoro-benzoyl)-urea    (Chlorfluazuron), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 213;-   (X) O,O-diethyl-O-3,5,6-trichloro-2-pyridyl-phosphorothioate    (Chlorpyrifos), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 235;-   (XI)    (RS)-α-cyano-4-fluoro-3-phenoxybenzyl-(1RS,3RS1RS,3RS)-3-(2,2-dichlorovinyl)2,2-di-methylcyclopropanecarboxylate    (Cyfluthrin), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 293;-   (XII) Mixture of    (S)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoro-propenyl)-2,2-dimethylcyclopropanecarboxylate    and    (R)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate    (Lambda-Cyhalothrin), from The Pesticide Manual, 11^(th) Ed. (1997),    The British Crop Protection Council, London, page 300;-   (XIII) Racemate consisting of    (S)-α-cyano-3-phenoxybenzyl-(Z)-(1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate    and    (R)-α-cyano-3-phenoxybenzyl-(1S,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate    (Alpha-cypermethrin), from The Pesticide Manual, 11^(th) Ed. (1997),    The British Crop Protection Council, London, page 308;-   (XIV) a mixture of the stereoisomers of (S)-α-cyano-3-phenoxybenzyl    (1RS,3RS,1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate    (zeta-Cypermethrin), from The Pesticide Manual, 11^(th) Ed. (1997),    The British Crop Protection Council, London, page 314;-   (XV)    (S)-α-cyano-3-phenoxybenzyl-(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane-carboxylate    (Deltamethrin), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 344;-   (XVI) (4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea (Diflubenzuron),    from The Pesticide Manual, 11^(th) Ed. (1997), The British Crop    Protection Council, London, page 395;-   (XVII)    (1,4,5,6,7,7-Hexachloro-8,9,10-trinorborn-5-en-2,3-ylenebismethylene)-sulphite    (Endosulfan), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 459;-   (XVIII) α-ethylthio-o-tolyl-methylcarbamate (Ethiofencarb), from The    Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection    Council, London, page 479;-   (XIX) O,O-dimethyl-O-4-nitro-m-tolyl-phosphorothioate    (Fenitrothion), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 514;-   (XX) 2-sec-butylphenyl-methylcarbamate (Fenobucarb), from The    Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection    Council, London, page 516;-   (XXI)    (RS)-α-cyano-3-phenoxybenzyl-(RS)-2-(4-chlorophenyl)-3-methylbutyrate    (Fenvalerate), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 539;-   (XXII)    S-[formyl(methyl)carbamoylmethyl]-O,O-dimethyl-phosphorodithioate    (Formothion), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 625;-   (XXIII) 4-Methylthio-3,5-xylyl-methylcarbamate (Methiocarb), from    The Pesticide Manual, 11^(th) Ed. (1997), The British Crop    Protection Council, London, page 813;-   (XXIV) 7-Chlorobicyclo[3.2.0]hepta-2,6-dien-6-yl-dimethylphosphate    (Heptenophos), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 670;-   (XXV) 1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylidenamine    (Imidacloprid), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 706;-   (XXVI) 2-isopropylphenyl-methylcarbamate (Isoprocarb), from The    Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection    Council, London, page 729;-   (XXVII) O,S-dimethyl-phosphoramidothioate (Methamidophos), from The    Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection    Council, London, page 808;-   (XXVIII) S-Methyl-N-(methylcarbamoyloxy)thioacetimidate (Methomyl),    from The Pesticide Manual, 11^(th) Ed. (1997), The British Crop    Protection Council, London, page 815;-   (XXIX) Methyl-3-(dimethoxyphosphinoyloxy)but-2-enoate (Mevinphos),    from The Pesticide Manual, 11^(th) Ed. (1997), The British Crop    Protection Council, London, page 844;-   (XXX) O,O-diethyl-O-4-nitrophenyl-phosphorothioate (Parathion), from    The Pesticide Manual, 11^(th) Ed. (1997), The British Crop    Protection Council, London, page 926;-   (XXXI) O,O-dimethyl-O-4-nitrophenyl-phosphorothioate    (Parathion-methyl), from The Pesticide Manual, 11^(th) Ed. (1997),    The British Crop Protection Council, London, page 928;-   (XXXII)    S-6-chloro-2,3-dihydro-2-oxo-1,3-benzoxazol-3-ylmethyl-O,O-diethyl-phosphor-dithioate    (Phosalone), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 963;-   (XXXIII)    2-Dimethylamino-5,6-dimethylpyrimidin-4-yl-dimethylcarbamate    (Pirimicarb), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 985;-   (XXXIV) 2-isopropoxyphenyl-methylcarbamate (Propoxur), from The    Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection    Council, London, page 1036;-   (XXXV)    1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea    (Teflubenzuron), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 1158;-   (XXXVI) S-tert-butylthiomethyl-O,O-dimethyl-phosphorodithioate    (Terbufos), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 1165;-   (XXXVII)    ethyl-(3-tert.-butyl-1-dimethylcarbamoyl-1H-1,2,4-triazol-5-yl-thio)-acetate,    (Triazamate), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 1224;-   (XXXVIII) Abamectin, from The Pesticide Manual, 11^(th) Ed. (1997),    The British Crop Protection Council, London, page 3;-   (XXXIX) 2-sec-butylphenyl-methylcarbamate (Fenobucarb), from The    Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection    Council, London, page 516;-   (XL) N-tert.-butyl-N′-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide    (Tebufenozide), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 1147;-   (XLI) (±)-5-amino-1-(2,6-dichloro    α,α,α-4-trifluoro-p-tolyl)4-trifluoromethyl-sulphinylpyrazol-3-carbonitrile    (Fipronil), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 545;-   (XLII)    (RS)-α-cyano-4-fluoro-3-phenoxybenzyl(1RS,3RS,1RS,3RS)3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate    (beta-Cyfluthrin), from The Pesticide Manual, 11^(th) Ed. (1997),    The British Crop Protection Council, London, page 295;-   (XLIII)    (4-ethoxyphenyl)-[3-(4-fluoro-3-phenoxyphenyl)propyl](dimethyl)silane    (Silafluofen), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 1105;-   (XLIV) tert.-butyl    (E)-α-(1,3-dimethyl-5-phenoxypyrazol-4-yl-methylenamino-oxy)-p-toluate    (Fenpyroximate), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 530;-   (XLV)    2-tert.-butyl-5-(4-tert.-butylbenzylthio)-4-chloropyridazin-3(2H)-one    (Pyridaben), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 1161;-   (XLVI) 4-[[4-(1,1-dimethylphenyl)phenyl]ethoxy]-quinazoline    (Fenazaquin), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 507;-   (XLVII) 4-phenoxyphenyl-(RS)-2-(pyridyloxy)propyl-ether    (Pyriproxyfen), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 1073;-   (XLVIII)    5-chloro-N-{2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethyl}-6-ethylpyrimidine-4-amine    (Pyrimidifen), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 1070;-   (XLIX)    (E)-(6-chloro-3-pyridylmethyl)-N-ethyl-N′-methyl-2-nitrovinylidenediamine    (Nitenpyram), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 880;-   (L)    (E)-N¹-[(6-chloro-3-pyridyl)methyl]-N²-cyano-N¹-methylacetamidine    (NI-25, Acetamiprid), from The Pesticide Manual, 11^(th) Ed. (1997),    The British Crop Protection Council, London, page 9;-   (LI) Avermectin B₁, from The Pesticide Manual, 11^(th) Ed. (1997),    The British Crop Protection Council, London, page 3;-   (LII) an insect-active extract from a plant, especially    (2R,6aS,12aS)-1,2,6,6a,12,12a-hexhydro-2-isopropenyl-8,9-dimethoxy-chromeno[3,4-b]furo[2,3-h]chromen-6-one    (Rotenone), from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 1097; and an extract    from Azadirachta indica, especially azadirachtin, from The Pesticide    Manual, 11^(th) Ed. (1997), The British Crop Protection Council,    London, page 59; and-   (LIII) a preparation which contains insect-active nematodes,    preferably Heterorhabditis bacteriophora and Heterorhabditis    megidis, from The Pesticide Manual, 11^(th) Ed. (1997), The British    Crop Protection Council, London, page 671; Steinemema feltiae, from    The Pesticide Manual, 11^(th) Ed. (1997), The British Crop    Protection Council, London, page 1115 and Steinemema scapterisci,    from The Pesticide Manual, 11^(th) Ed. (1997), The British Crop    Protection Council, London, page 1116;-   (LIV) a preparation obtainable from Bacillus subtilis, from The    Pesticide Manual, 11^(th) Ed. (1997), The British Crop Protection    Council, London, page 72; or from a strain of Bacillus thuringiensis    with the exception of compounds isolated from GC91 or from    NCTC11821; The Pesticide Manual, 11^(th) Ed. (1997), The British    Crop Protection Council, London, page 73;-   (LV) a preparation which contains insect-active fungi, preferably    Verticillium lecanii, from The Pesticide Manual, 11^(th) Ed. (1997),    The British Crop Protection Council, London, page 1266; Beauveria    brogniartii, from The Pesticide Manual, 11^(th) Ed. (1997), The    British Crop Protection Council, London, page 85 and Beauveria    bassiana, from The Pesticide Manual, 11^(th) Ed. (1997), The British    Crop Protection Council, London, page 83;-   (LVI) a preparation which contains insect-active viruses, preferably    Neodipridon Sertifer NPV, from The Pesticide Manual, 11^(th) Ed.    (1997), The British Crop Protection Council, London, page 1342;    Mamestra brassicae NPV, from The Pesticide Manual, 11^(th) Ed.    (1997), The British Crop Protection Council, London, page 759 and    Cydia pomonella granulosis virus, from The Pesticide Manual, 11^(th)    Ed. (1997), The British Crop Protection Council, London, page 291;-   (CLXXXI)    7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxyphenyl)-carbamoyl]indol[1,2e]oxazoline-4a-carboxylate    (DPX-MP062, Indoxycarb), from The Pesticide Manual, 11^(th) Ed.    (1997), The British Crop Protection Council, London, page 453;-   (CLXXXII)    N′-tert.-butyl-N′-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide    (RH-2485, Methoxyfenozide), from The Pesticide Manual, 11^(th) Ed.    (1997), The British Crop Protection Council, London, page 1094; and-   (CLXXXIII) (N′L[methoxy-biphenyl-3-yl]-hydrazinecarboxylic acid    isopropylester (D 2341), from Brighton Crop Protection Conference,    1996, 487-493;-   (R2) Book of Abstracts, 212th ACS National Meeting Orlando, Fla.,    August 25-29 (1996), AGRO-020. Publisher American Chemical Society,    Washington, D.C. CONEN: 63BFAF.

As a consequence of the above details, a further essential aspect of thepresent invention relates to combination preparations for the control ofparasites on warm-blooded animals, characterised in that they contain,in addition to a compound of formula I, at least one further activeingredient having the same or different sphere of activity and at leastone physiologically acceptable carrier. The present invention is notrestricted to two-fold combinations.

As a rule, the anthelminthic compositions according to the inventioncontain 0.1 to 99% by weight, especially 0.1 to 95% by weight of activeingredient of formula I, Ia or mixtures thereof, 99.9 to 1% by weight,especially 99.8 to 5% by weight of a solid or liquid admixture,including 0 to 25% by weight, especially 0.1 to 25% by weight of asurfactant.

Application of the compositions according to the invention to theanimals to be treated may take place topically, perorally, parenterallyor subcutaneously, the composition being present in the form ofsolutions, emulsions, suspensions, (drenches), powders, tablets, boli,capsules and pour-on formulations.

The pour-on or spot-on method consists in applying the compound offormula I to a specific location of the skin or coat, advantageously tothe neck or backbone of the animal. This takes place e.g. by applying aswab or spray of the pour-on or spot-on formulation to a relativelysmall area of the coat, from where the active substance is dispersedalmost automatically over wide areas of the fur owing to the spreadingnature of the components in the formulation and assisted by the animal'smovements.

Pour-on or spot-on formulations suitably contain carriers, which promoterapid dispersement over the skin surface or in the coat of the hostanimal, and are generally regarded as spreading oils. Suitable carriersare e.g. oily solutions; alcoholic and isopropanolic solutions such assolutions of 2-octyldodecanol or oleyl alcohol; solutions in esters ofmonocarboxylic acids, such as isopropyl myristate, isopropyl palmitate,lauric acid oxalate, oleic acid oleyl ester, oleic acid decyl ester,hexyl laurate, oleyl oleate, decyl oleate, capric acid esters ofsaturated fat alcohols of chain length C₁₂-C₁₈; solutions of esters ofdicarboxylic acids, such as dibutyl phthalate, diisopropyl isophthalate,adipic acid diisopropyl ester, di-n-butyl adipate or also solutions ofesters of aliphatic acids, e.g. glycols. It may be advantageous for adispersing agent to be additionally present, such as one known from thepharmaceutical or cosmetic industry. Examples are 2-pyrrolidone,2-(N-alkyl)pyrrolidone, acetone, polyethylene glycol and the ethers andesters thereof, propylene glycol or synthetic triglycerides.

The oily solutions include e.g. vegetable oils such as olive oil,groundnut oil, sesame oil, pine oil, linseed oil or castor oil. Thevegetable oils may also be present in epoxidised form. Paraffins andsilicone oils may also be used.

A pour-on or spot-on formulation generally contains 1 to 20% by weightof a compound of formula I, 0.1 to 50% by weight of dispersing agent and45 to 98.9% by weight of solvent.

The pour-on or spot-on method is especially advantageous for use on herdanimals such as cattle, horses, sheep or pigs, in which it is difficultor time-consuming to treat all the animals orally or by injection.Because of its simplicity, this method can of course also be used forall other animals, including individual domestic animals or pets, and isgreatly favoured by the keepers of the animals, as it can often becarried out without the specialist presence of the veterinarian.

Whereas it is preferred to formulate commercial products asconcentrates, the end user will normally use dilute formulations.

Such compositions may also contain further additives, such asstabilisers, anti-foaming agents, viscosity regulators, binding agentsor tackifiers, as well as other active ingredients, in order to achievespecial effects.

Anthelminthic compositions of this type, which are used by the end user,similarly form a constituent of the present invention.

In each of the processes according to the invention for pest control orin each of the pest control compositions according to the invention, theactive ingredients of formula I can be used in all of their stericconfigurations or in mixtures thereof.

The invention also includes a method of prophylactically protectingwarm-blooded animals, especially productive livestock, domestic animalsand pets, against parasitic helminths, which is characterised in thatthe active ingredients of formula I or the active ingredientformulations prepared therefrom are administered to the animals as anadditive to the feed, or to the drinks or also in solid or liquid form,orally or by injection or parenterally. The invention also includes thecompounds of formula I according to the invention for usage in one ofthe said processes.

The following examples serve merely to illustrate the invention withoutrestricting it, the term active ingredient representing a substancelisted in tables 1 to 3.

In particular, preferred formulations are made up as follows:

(%=percent by weight)

FORMULATION EXAMPLES

a) b) active ingredient from tables 1 and 2  5% 10% kaolin 94% — highlydispersed silicic acid  1% — attapulgite — 90%

The active ingredient is dissolved in methylene chloride, sprayed ontothe carrier and the solvent subsequently concentrated by evaporationunder vacuum. Granulates of this kind can be mixed with the animal feed.

2. Granulate

active ingredient from tables 1 and 2  3% polyethylene glycol (mw 200) 3% kaolin 94% (mw = molecular weight)

The finely ground active ingredient is evenly applied in a mixer to thekaolin which has been moistened with polyethylene glycol. In this way,dust-free coated granules are obtained.

3. Tablets or Boli

I active ingredient from tables 1 and 2 33.00% methylcellulose 0.80%silicic acid, highly dispersed 0.80% corn starch 8.40% II lactose,cryst. 22.50% corn starch 17.00% microcryst. cellulose 16.50% magnesiumstearate 1.00%

-   I Methyl cellulose is stirred into water. After the material has    swollen, silicic acid is stirred in and the mixture homogeneously    suspended. The active ingredient and the corn starch are mixed. The    aqueous suspension is worked into this mixture and kneaded to a    dough. The resulting mass is granulated through a 12 M sieve and    dried.-   II All 4 excipients are mixed thoroughly.-   III The preliminary mixes obtained according to I and II are mixed    and pressed into tablets or boli.    4. Injectables

A. Oily Vehicle (Slow Release)

1. active ingredient from tables 1 and 2 0.1-1.0 g groundnut oil ad 100ml 2. active ingredient from tables 1 and 2 0.1-1.0 g sesame oil ad 100ml

Preparation: The active ingredient is dissolved in part of the oilwhilst stirring and, if required, with gentle heating, then aftercooling made up to the desired volume and sterile-filtered through asuitable membrane filter with a pore size of 0.22 mm.

B Water-Miscible Solvent (Average Rate of Release)

active ingredient from tables 1 and 2 0.1-1.0 g4-hydroxymethyl-1,3-dioxolane (glycerol formal) 40 g 1,2-propanediol ad100 ml An active ingredient from table 1 0.1-1.0 g glycerol dimethylketal 40 g 1,2-propanediol ad 100 ml

Preparation: The active ingredient is dissolved in part of the solventwhilst stirring, made up to the desired volume and sterile-filteredthrough a suitable membrane filter with a pore size of 0.22 mm.

C. Aqueous Solubilisate (Rapid Release)

1. active ingredient from tables 1 and 2 0.1-1.0 g polyethoxylatedcastor oil (40 ethylene oxide units) 10 g 1,2-propanediol 20 g benzylalcohol 1 g aqua ad inject. ad 100 ml 2. active ingredient from tables 1and 2 0.1-1.0 g polyethoxylated sorbitan monooleat 8 g (20 ethyleneoxide units) 4-hydroxymethyl-1,3-dioxolane (glycerol formal) 20 g benzylalcohol 1 g aqua ad inject. ad 100 ml

Preparation: The active ingredient is dissolved in the solvents and thesurfactant, and made up with water to the desired volume. Sterilefiltration through an appropriate membrane filter of 0.22 mm pore size.

5. Pour On

A. active ingredient from tables 1 and 2 5 g isopropyl myristate 10 gisopropanol ad 100 ml B active ingredient from tables 1 and 2 2 g hexyllaurate 5 g medium-chained triglyceride 15 g ethanol ad 100 ml C. activeingredient from tables 1 and 2 2 g oleyl oleate 5 g N-methylpyrrolidone40 g isopropanol ad 100 ml

The aqueous systems may also preferably be used for oral and/orintraruminal application.

The compositions may also contain further additives, such asstabilisers, e.g. where appropriate epoxidised vegetable oils(epoxidised coconut oil, rapeseed oil, or soybean oil); antifoams, e.g.silicone oil, preservatives, viscosity regulators, binders, andtackifiers, as well as fertilisers or other active ingredients toachieve special effects.

Further biologically active substances or additives, which are neutraltowards the compounds of formula I and do not have a harmful effect onthe host animal to be treated, as well as mineral salts or vitamins, mayalso be added to the described compositions.

Biological Examples 1. In-vivo test on Trichostrongylus colubriformisand Haemonchus contortus on Mongolian Gerbils (Meriones unguiculatus)Using Peroral Application

Six to eight week old Mongolian gerbis are infected by artificialfeeding with ca. 2000 third instar larvae each of T. colubriformis andH. contortus. 6 days after infection, the gerbils are lightlyanaesthetised with N₂O and treated by peroral application with the testcompounds, dissolved in a mixture of 2 parts DMSO and 1 partpolyethylene glycol (PEG 300), in quantities of 100, 32 and 10-0.1mg/kg. On day 9 (3 days after treatment), when most of the H. contortusthat are still present are late 4th instar larvae and most of the T.colubriformis are immature adults, the gerbils are killed in order tocount the worms. The efficacy is calculated as the % reduction of thenumber of worms in each gerbil, compared with the geometric average ofnumber of worms from 8 infected and untreated gerbils.

In this test, a vast reduction in nematode infestation is achieved withcompounds of formula I.

1. A method of controlling Haemonchus contortus and Trichostrongyluscolubriformis helminthes in warm-blooded domestic animals comprisingadministering a composition to said domestic animals, wherein saidcomposition comprises a pesticidally active amount of the compound ofthe formula

and optionally enantiomers thereof.
 2. A method of controllinghelminthes in domestic animals comprising administering a composition tosaid domestic animals, wherein said composition comprises a pesticidallyactive amount of a compound of the formula

wherein R₂ signifies unsubstituted phenyl or phenyl mono- ordi-substituted by R₅; n is 0 or 1; R₁ is methylene which is substitutedby unsubstituted phenyloxy or phenyloxy mono- or disubstituted by R₅,whereby the substituents may be the same as one another or different ifthe number thereof is greater than 1; and R₅ signifieshalogen-C₁-C₆-alkyl, halogen-C₁-C₆-alkenyl, halogen-C₁-C₆-alkynyl, orhalogen.
 3. The method of claim 2 wherein said helminthes areendoparasitic nematodes.
 4. The method of claim 3 wherein saidendoparasitic nematodes are selected from the group consisting ofHaemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia,Ascaris, Bunostonum, Oesophagostonum, Charbertia, Trichuris, Strongylus,Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia,Oxyuris, Ancylostoma, Uncinaria, Toxascaris, and Paracaris.